Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2009(6): 935-940
DOI: 10.1055/s-0028-1087975
DOI: 10.1055/s-0028-1087975
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Quinonoid Analogues of Diospyrin
Further Information
Received
22 August 2008
Publication Date:
24 February 2009 (online)
Publication History
Publication Date:
24 February 2009 (online)
Abstract
Diospyrin and its analogues have been known for their antimycobacterial properties. Significant efforts have been made towards the synthesis of structural analogues of diospyrin with improved biological activities. We report here the synthesis of four novel analogues of diospyrin via a Suzuki cross coupling between bromonaphthoquinones and aryl- or naphthylboronic acids in the presence of tetrakis(triphenylphosphine)palladium(0) as catalyst, followed by selective demethylation of the intermediates.
Key words
quinones - biaryls - boronic acids - diospyrin - Suzuki coupling
- 1
Shakya R.Rao BS.Shrestha B. Ann. Pharmacother. 2004, 38: 1074 - 2
Besra GS.Kremer LS. Expert Opin. Investig. Drugs 2002, 11: 1033 - 3
Morton RA. Biochemistry of Quinones Academic Press; New York: 1965. - 4
Nohl H.Jordan W.Youngman RI. Adv. Free Radical Biol. Med. 1986, 2: 211 - 5
Meganathan R. Vitam. Horm. 2001, 61: 173 - 6
Kersten W. Prog. Mol. Subcell. Biol. 1971, 2: 48 - 7
Olenick CG.Hahn FE. Ann. N. Y. Acad. Sci. 1974, 235: 542 - 8
Pardee AB.Li YZ.Li CJ. Curr. Cancer Drug Targets 2002, 2: 227 - 9
Lall N.Meyer JJM. J. Ethnopharmacol. 2000, 72: 313 - 10
Sidhu GS.Pardhasaradhi M. Indian J. Chem. 1970, 8: 569 - 11
Harrison WTA.Musgrave OC. Acta. Crystallogr., Sect. C 2004, 60: 399 - 12
Yoshida M.Mori K. Eur. J. Org. Chem. 2000, 1313 - 13
Lall N.Sarma MD.Hazra B.Meyer JJM. J. Antimicrob. Chemother. 2003, 51: 435 - 14
Adeniyi BA.Fong HHS.Pezzuto JM.Luyengi L.Odelola HA. Phytother. Res. 2000, 14: 112 - 15
Tran T.Saheba E.Arcerio AV.Chavez V.Li Q.Martinez LE.Primm TP. Bioorg. Med. Chem. 2004, 12: 4809 - 16
Alvarado PL.Avendano C.Menendez JC. Synth. Commun. 2002, 32: 3233 -
17a
Banville J.Brassard P. J. Chem. Soc., Perkin Trans. 1 1976, 1852 -
17b
Cameron DW.Feutrill GI.Hodder DJ. J. Chem. Soc., Chem. Commun. 1978, 688 -
17c
Savard J.Brassard P. Tetrahedron Lett. 1979, 20: 4911 -
17d
Cameron DW.Conn C.Feutrill GI. Aust. J. Chem. 1981, 34: 1945 - 18
Ho TI.Chen GP.Lin YC.Lin YM.Chen FC. Phytochemistry 1986, 25: 1988 - 19
Kesteleyn B.De Kimpe N.Puyrelde LV. J. Org. Chem. 1999, 64: 1173 - 20
Jung ME.Hagenah JA. J. Org. Chem. 1987, 52: 1889 - 21
Maddaford SP.Keay BA. J. Org. Chem. 1994, 59: 6501 - 22
Miyaura N.Suzuki A. Chem. Rev. 1995, 95: 2457 - 23
Syper L.Kloc K.Mlochowski J.Szulc Z. Synthesis 1979, 521 - 24
Inaba T.Umezawa I.Yuasa M.Inoue T.Mihashi S.ItokawaH .Ogura K. J. Org. Chem. 1987, 52: 2957 - 25
He Z.Craig DC.Colbran SB. J. Chem. Soc., Dalton Trans. 2002, 4224